Entire home

~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.

Photo gallery for ~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.

Private pool with sitting pool and tranquil waterfall!!
Welcome to Tropical Dream. What a lovely home!
This is Key West luxury!
Welcome to Tropical Dream!
Amazing open concept for entertaining!

Reviews

9.4 out of 10
Exceptional
4 bedrooms4+ bathroomsSleeps 8185.8 sq m

Popular amenities

  • Dryer
  • Washer
  • Pet-friendly
  • Parking available
  • Kitchen
  • Pool

Explore the area

Map
Key West, Florida
  • Duval Street
    ‪7 min walk‬
  • Ernest Hemingway Home and Museum
    ‪15 min walk‬
  • Mallory Square
    ‪17 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 Queen Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Single Beds

4 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet

Bathroom 3

Bathtub · Toilet · Shower only

Bathroom 4

Bathtub or shower · Toilet

Bathroom 5

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Balcony

About this property

~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!

THE PROPERTY: As you enter the carport and begin to unwind, you will be greeted by beautiful porches and tropical greenery. Drop your luggage at the door and go for a swim. Around back, a private pool with waterfall feature awaits you. Later, you can cozy up to a bedroom of your choice.

The first-floor queen ensuite bedroom includes a desk, dresser, ceiling fan and access to the pool. The second floor is home to three additional bedrooms. The first is a king suite with TV, wet bar, and walk-in/walk-through closet with access to the washer/dryer. Its ensuite bath has a large soaking tub with a laminar flow filler that fills from the ceiling, and a spacious walk-in shower with multiple heads. The room also provides access to a private balcony. The second is a queen suite with nightstands, ceiling fan, TV, dresser, and glass doors leading to the sun deck. The third bedroom on the second floor includes twin beds that may be converted to a king. This bedroom accesses a full bath from the hallway. It also has access to the second-floor balcony in front of the home that overlooks Fleming Street. This balcony wraps around the side of the house and connects to the sun deck. Its spiral stairs will lead you down to the pool area.

Back downstairs you will pass the half bath on your way to the open concept great room. Here you will find sunshine, happiness and the home’s living room and kitchen. Stainless steel appliances, a triple sink, and granite counters round out the gourmet kitchen. The adjoining living room has a queen sleeper sofa, plenty of seating for your family and friends, a large screen TV, ceiling fans, and storage. From this area you will also find table seating for six, a wet bar with wine fridge, and access to the pool area via the expansive wall of windows. This home embodies the Key West lifestyle and is yours to enjoy while here on the island.

BED CONFIGURATION: This home has 4 beautifully appointed bedrooms. A queen ensuite bedroom is located on the first floor for those who may not prefer stairs. Three additional bedrooms are located on the second floor. They include one king ensuite, one queen ensuite and one twin bedroom. The twin beds may be converted to a king size bed and have access to a full bath in the hall.

OUTDOOR AMENITIES: A small sitting pool spills into the larger pool with waterfall feature and will cool you down after a day exploring the island. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. There is a deck and outdoor dining area for al fresco meals.

PARKING: There is designated parking for 2 vehicles in the carport.

LOCATION: Old Town, North of Truman. Many tourist attractions are located here as well as restaurants, shops, and galleries. Just 5 blocks to Duval Street or the Marina and walkable for those who like to park their car and chill. The neighborhood boasts historic homes, shotgun, and conch style homes.

PETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats not allowed.

SMOKING: This is a non-smoking home.

***Guests must be 25 years of age or older unless accompanied by an adult.

***Please note that the cleaning fee includes a full "mid-stay" clean***

***Managed by Historic Key West Vacation Rentals***

Property manager

Historic Key West Vacation Rentals
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed
default

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Key West

Located in Key West, this holiday home is in the city centre. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.
Map
Key West, Florida

What's nearby

  • Duval Street - 7 min walk - 0.7 km
  • Ernest Hemingway Home and Museum - 15 min walk - 1.3 km
  • Mallory Square - 17 min walk - 1.5 km
  • Southernmost Point - 4 min drive - 2.1 km
  • South Beach - 8 min drive - 2.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 9 min drive

Restaurants

  • ‪The Waterfront Brewery - ‬6 min walk
  • ‪Cuban Coffee Queen - ‬5 min walk
  • ‪Conch Republic Seafood Company - ‬9 min walk
  • ‪Kermit's Key West Key Lime Shoppe - ‬9 min walk
  • ‪Schooner Wharf Bar - ‬7 min walk

Frequently asked questions

Does ~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town. have a pool?

Yes, this property has a pool.

Is ~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town. pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at ~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.?

Check-in begins at 4:00 PM.

What time is check-out at ~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.?

Checkout is at 10:00 AM.

Where is ~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town. located?

Located in Old Town Key West, this holiday home is within a 10-minute walk of The Kite House and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 1 mile (2 km).

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 17 out of 23 reviews
Rating 8 - Good. 4 out of 23 reviews
Rating 6 - Okay. 2 out of 23 reviews
Rating 4 - Poor. 0 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Roger P.

Wonderful Keys Rental Property

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very positive stay in all regards. Has all the necessary amenities. Very pleasant patio area. Great location. Quiet but easy walk up to Duval or harbor area.
This review comes from a trusted partner site and has not been verified.

8/10 Good

Vivian M.

Tropical Dream

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a great time at the place.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Penny O.

Best rental property EVER

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I’ve been renting in key west for 7 years and this is by far the best rental property I’ve had!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

william p.

Escape to Paradise

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Wonderful home in a great location. Easy walk to some great neighborhood restaurants. Plenty of room for all. The folks at Historic Key West Rentals were very responsive and accommodating. Have used them several times before with no issues or disappointments. Will reach out to them again for our next visit. Miss Key West already.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Dan E.

Wonderful Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a great time at this wonderful house. Perfect location, great space, and all the amenities. Great to be able to easily park and close enough to everything that we never moved the car again after. Porches are great for people watching. The few issues we had were quickly dealt with by the great team at HKWVR. Can't wait to come back next time I can justify leaving home for a month :)

10/10 Excellent

Royal B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Near perfect Key West vacation

Excellent property in great location. Spacious 4 BR 4BA. Well equipped. Nice plunge pool. 2 parking spaces a rare find to accommodate car and golf cart. Management company was extraordinarily responsive. Only complaint is with the lumpy mattresses.
Stayed 28 nights in Feb 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kim H.

Great stay in a great location!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Thoroughly enjoyed our month long stay at Tropical Dream. The location is very convenient (a few blocks to Duval, the market and several great restaurants). All beds were comfy and we had everything we needed for a pleasant stay. The patio was small but the pool was cool, which was a big plus for a hot June/July stay. Would definitely stay here again.
This review comes from a trusted partner site and has not been verified.

8/10 Good

906 Fleming

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great experience, nice home in a great location. Management company was outstanding .
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Helping in a crisis

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I rented a home in Key West Florida when Hurricane Irma struck...I was there with 90 year old parents and a large black lab. Historic Key West Vacations went out of their way to encourage us to evacuate before the mass evacuations and probably helped to save my parents lives....I cannot say enough about their concern and SMART advise...
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Wonderful Summer in Key West!!!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Could not possibly say enough good things about our 10 week stay in Key West this past summer but will try to point out a few of the more outstanding features! First, hats off to my new friend Thomas Lane at Historic Key West Vacation Rentals! Since my wife and I were pretty much moving to Key West for the summer there were a host of questions I had for the six months prior to our arrival and Thomas was always readily available to answer all of them! As a corollary thereto let me say that when we arrived, we received that same standard of service as whatever questions/issues we had were immediately addressed! Second, my hats are off to the owners of 906 Fleming as well! The AC units were getting a little long in the tooth and were struggling a bit with the heat and after diligent follow up by the guys at HKWV without further hesitation the Owner replaced both units and HKWV even gave us a gift certificate to a (very fine) local restaurant for our trouble. That's the way a first class operation works! Third, if you are not familiar with Key West as a couple that has spent a lot of time there (including the 10 weeks straight we just returned from) 906 Fleming could not possible be more perfectly located! Fleming is within about three blocks of the marina and easy walking distance to Duval and Starbucks (an every morning venture for me and my wife I might add) and there is even a super nice and surprisingly large grocery store (Faustos) right down the street in addition to the all organic boutique store directly across the street such that the wife and I probably did not get in the jeep to drive somewhere maybe 5-6 times the entirety of our stay. Also, Fleming is a one way street and though it is very close to pretty much anything that you might want to go visit (even over the course of 10 weeks) it has very little traffic which makes walking it everyday feel like a Sunday morning stroll down the streets of an old southern town like Charleston for example!!!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Searing M.

Tropical Dream Monthly Rental

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our family rented Tropical Dream for July 2018. The home was very well located in Old Town. The location to Key West Bight Marina, off street parking and pool were critical amenities for our family. We easily walked everywhere despite having brought bikes. The home was clean and well appointed for our family of five plus three extra friends. We had an issue with the water not working in one bathroom and the management company immediately replaced the faucet. We would definitely recommend Tropical Dream as well as KW Historic Rentals as a management company.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

A guest from Miami Beach, FL

Wonderful getaway!!!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We stayed for one marvelous month and wish we could have stayed longer. The home was perfectly situated in the heart of Old Town. It is FULLY equipped with everything you could possibly need and want. From kitchen supplies to bed linens and BBQ tools - everything was perfect! As far as the rental company, I can’t say enough good things about these ladies! They are marvelous! Our BBQ was not working one day, so they gave us a gift card to the lovely restaurant down the street to enjoy while the repair was underway. If you’re on the fence don’t be! You will not be disappointed. For reference, this glowing review is coming from two very picky frequent travelers who only write reviews in response to terrible experiences. That's how much we enjoyed our time at Tropical Dream. Perfect home and perfect service! 10 stars.
This review comes from a trusted partner site and has not been verified.

6/10 Okay

april t.

winter rental

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Key west has great weather, the house was nice. If you plan on cooking bring your own pans, very few and old and damaged. The sitting area in the living room only accommodates 5 adults but house sleeps eight. I would purchase a pit with more sitting. Location noisy at night a lot of street walking and talking late at night. pool was great.
This review comes from a trusted partner site and has not been verified.

6/10 Okay

april t.

winter rental

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Key west has great weather, the house was nice. If you plan on cooking bring your own pans, very few and old and damaged. The sitting area in the living room only accommodates 5 adults but house sleeps eight. I would purchase a pit with more sitting. Location noisy at night a lot of street walking and talking late at night. pool was great.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

A guest from Miami Beach, FL

Wonderful getaway!!!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We stayed for one marvelous month and wish we could have stayed longer. The home was perfectly situated in the heart of Old Town. It is FULLY equipped with everything you could possibly need and want. From kitchen supplies to bed linens and BBQ tools - everything was perfect! As far as the rental company, I can’t say enough good things about these ladies! They are marvelous! Our BBQ was not working one day, so they gave us a gift card to the lovely restaurant down the street to enjoy while the repair was underway. If you’re on the fence don’t be! You will not be disappointed. For reference, this glowing review is coming from two very picky frequent travelers who only write reviews in response to terrible experiences. That's how much we enjoyed our time at Tropical Dream. Perfect home and perfect service! 10 stars.

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winter Getaway

Great house and great location. We enjoyed our stay so much we are coming back next year.
Stayed 28 nights in Feb 2020
This review comes from a trusted partner site and has not been verified.

8/10 Good

906 Fleming

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great experience, nice home in a great location. Management company was outstanding .
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Searing M.

Tropical Dream Monthly Rental

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our family rented Tropical Dream for July 2018. The home was very well located in Old Town. The location to Key West Bight Marina, off street parking and pool were critical amenities for our family. We easily walked everywhere despite having brought bikes. The home was clean and well appointed for our family of five plus three extra friends. We had an issue with the water not working in one bathroom and the management company immediately replaced the faucet. We would definitely recommend Tropical Dream as well as KW Historic Rentals as a management company.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Wonderful Summer in Key West!!!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Could not possibly say enough good things about our 10 week stay in Key West this past summer but will try to point out a few of the more outstanding features! First, hats off to my new friend Thomas Lane at Historic Key West Vacation Rentals! Since my wife and I were pretty much moving to Key West for the summer there were a host of questions I had for the six months prior to our arrival and Thomas was always readily available to answer all of them! As a corollary thereto let me say that when we arrived, we received that same standard of service as whatever questions/issues we had were immediately addressed! Second, my hats are off to the owners of 906 Fleming as well! The AC units were getting a little long in the tooth and were struggling a bit with the heat and after diligent follow up by the guys at HKWV without further hesitation the Owner replaced both units and HKWV even gave us a gift certificate to a (very fine) local restaurant for our trouble. That's the way a first class operation works! Third, if you are not familiar with Key West as a couple that has spent a lot of time there (including the 10 weeks straight we just returned from) 906 Fleming could not possible be more perfectly located! Fleming is within about three blocks of the marina and easy walking distance to Duval and Starbucks (an every morning venture for me and my wife I might add) and there is even a super nice and surprisingly large grocery store (Faustos) right down the street in addition to the all organic boutique store directly across the street such that the wife and I probably did not get in the jeep to drive somewhere maybe 5-6 times the entirety of our stay. Also, Fleming is a one way street and though it is very close to pretty much anything that you might want to go visit (even over the course of 10 weeks) it has very little traffic which makes walking it everyday feel like a Sunday morning stroll down the streets of an old southern town like Charleston for example!!!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

George J.

Tropical Dream

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Excellent house. Excellent location. Excellent support from management staff. In stay complete cleaning was an added bonus.
Stayed 28 nights in Dec 2017
This review was submitted before 2018 and has not been verified.

8/10 Good

mark s.

Tropical dream

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Nice place, great location
Stayed 28 nights in Oct 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Helping in a crisis

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I rented a home in Key West Florida when Hurricane Irma struck...I was there with 90 year old parents and a large black lab. Historic Key West Vacations went out of their way to encourage us to evacuate before the mass evacuations and probably helped to save my parents lives....I cannot say enough about their concern and SMART advise...
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Kim H.

Great stay in a great location!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Thoroughly enjoyed our month long stay at Tropical Dream. The location is very convenient (a few blocks to Duval, the market and several great restaurants). All beds were comfy and we had everything we needed for a pleasant stay. The patio was small but the pool was cool, which was a big plus for a hot June/July stay. Would definitely stay here again.

About the host

Hosted by Historic Key West Vacation Rentals

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests